4-Benzyl-5-methyl-[1,4]oxazepan-3-one → 4-Benzyl-5-methyl-[1,4]oxazepane

HRID 515444ノート

反応式

HRID 515444 の反応式
[CH2:1]([N:8]1[CH:14]([CH3:15])[CH2:13][CH2:12][O:11][CH2:10][C:9]1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>O1CCCC1>[CH2:1]([N:8]1[CH:14]([CH3:15])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

3

反応物 1

HCID 584052534-Benzyl-5-methyl-[1,4]oxazepan-3-one

生成物 1

HCID 667187904-Benzyl-5-methyl-[1,4]oxazepane収率 100%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of 4-benzyl-5-methyl-[1,4]oxazepan-3-one (0.32 g, 1.4 mmol) in tetrahydrofuran (5 mL) was added 1M solution of boran-tetrahydrofran complex in tetrahydrofuran (5 mL, 5.0 mmol) dropwise at 0° C. under nitrogen atmosphere. The mixture was warmed to room temperature and stirred for 3 hours. Then the reaction was quenched by the addition of methanol and the solution was concentrated. The residual oil was dissolved in methanol (10 mL) and 1M sodium hydroxide aqueous solution was added at room temperature. The mixture was refluxed for 3 hours and diluted with water. Extraction with ethyl acetate was performed and the organic extracts were dried over anhydrous sodium sulfate. After evaporation of solvents, the residue was purified by flash column chromatography on silica gel to yield 4-benzyl-5-methyl-[1,4]oxazepane (0.30 g, 1.4 mmol, 100%) as colorless oil.

後処理

  1. customThen the reaction was quenched by the addition of methanol
  2. concentrationthe solution was concentrated
  3. dissolutionThe residual oil was dissolved in methanol (10 mL)
  4. addition1M sodium hydroxide aqueous solution was added at room temperature
  5. temperatureThe mixture was refluxed for 3 hours
  6. additiondiluted with water
  7. extractionExtraction with ethyl acetate
  8. dry with materialthe organic extracts were dried over anhydrous sodium sulfate
  9. customAfter evaporation of solvents
  10. customthe residue was purified by flash column chromatography on silica gel

出典と根拠

ORDレコード
ord-5dce31e93ef24052b61c4d955ee83513
出典データセット
uspto-grants-2015_08
特許番号
US09108957B2

反応ノート

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